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Persicogenin

Cat No.:V60101 Purity: ≥98%
Persicogenin can be extracted from Rhus retinorrhoea and has anti-cancer effect.
Persicogenin
Persicogenin Chemical Structure CAS No.: 28590-40-1
Product category: Plants
This product is for research use only, not for human use. We do not sell to patients.
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5mg
10mg
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Product Description
Persicogenin can be extracted from Rhus retinorrhoea and has anti-cancer effect.
Persicogenin (CAS 28590-40-1) is a naturally occurring O-methylated flavonoid, specifically a 5,3'-dihydroxy-7,4'-dimethoxyflavanone, isolated from various plant sources including Rhus retinorrhoea, Vitex trifolia L., and Lantana balansae. It exhibits a range of biological activities including anticancer, antimutagenic, antileishmanial, and antimycobacterial properties. Persicogenin inhibits the proliferation of cancer cells and mainly arrests the cell cycle at the G2/M phase in a dose-dependent manner. It also activates the Fas/Fas ligand apoptosis system.
Biological Activity I Assay Protocols (From Reference)
Targets
Persicogenin targets multiple pathways involved in cancer cell proliferation and survival. It inhibits the proliferation of mouse tsFT210 cancer cells and mainly arrests the cell cycle at the G2/M phase in a dose-dependent manner. The compound activates the Fas/Fas ligand apoptosis system, which is crucial for programmed cell death in cancer cells. Network pharmacology analysis has identified potential targets including EGFR, VEGFA, and ESR1, which are involved in various signaling pathways related to cancer and gastrointestinal health. Persicogenin also exhibits antileishmanial activity.
ln Vitro
In vitro, Persicogenin inhibits the proliferation of mouse tsFT210 cancer cells and mainly arrests the cell cycle at the G2/M phase in a dose-dependent manner. The compound exhibits moderate antimycobacterial activity against Mycobacterium tuberculosis with an MIC value of 174.8 μM. It also shows antileishmanial activity and anticancer activity. The compound activates the Fas/Fas ligand apoptosis system. These activities confirm Persicogenin's potential as a multi-target anticancer and antimicrobial agent.
ln Vivo
Specific in vivo data for Persicogenin are limited in the available literature. Given its in vitro anticancer activity and cell cycle arrest properties, the compound has potential for in vivo efficacy studies in mouse xenograft models of various cancers. Its antileishmanial activity suggests potential for in vivo studies in Leishmania infection models. Network pharmacology analysis suggests potential therapeutic effects in treating constipation, indicating possible applications in gastrointestinal research. However, specific published in vivo protocols are not available.
Enzyme Assay
The anticancer activity is assessed using cell proliferation assays. Mouse tsFT210 cancer cells or other cancer cell lines are cultured in appropriate media and treated with Persicogenin at various concentrations for 24-72 hours. Cell viability is measured using MTT, CCK-8, or CellTiter-Glo assays. Cell cycle distribution is analyzed by flow cytometry after propidium iodide staining, with the percentage of cells in G2/M phase determined. Apoptosis is assessed by measuring caspase-3/7 activity, Annexin V/PI staining, or DNA fragmentation. Fas/Fas ligand pathway activation is assessed by Western blot.
Cell Assay
For antimicrobial testing, Mycobacterium tuberculosis and other pathogens are cultured in appropriate media. Persicogenin is added at various concentrations, and bacterial growth is monitored by measuring optical density or by colony counting. The MIC is determined as the lowest concentration that inhibits visible growth. For antileishmanial activity, Leishmania parasites are cultured and treated with the compound, with parasite viability assessed using appropriate assays. Cytotoxicity in mammalian cells is assessed using standard viability assays.
Animal Protocol
In vivo studies for Persicogenin would be conducted in appropriate animal models. For anticancer activity, mouse xenograft models using cancer cell lines would be employed. The compound would be administered via oral gavage or intraperitoneal injection, and tumor volumes would be measured. For antileishmanial studies, Leishmania-infected mouse models would be used, with parasite burden and clinical signs assessed. For gastrointestinal studies, constipation models would be used to evaluate therapeutic effects. However, specific published protocols are not available.
ADME/Pharmacokinetics
Specific pharmacokinetic data for Persicogenin are not reported. As a flavonoid with moderate lipophilicity, the compound is expected to have reasonable oral absorption. The compound's molecular weight is approximately 316 g/mol. Pharmacokinetic studies would be required to determine parameters such as half-life, Cmax, oral bioavailability, and tissue distribution in animal models. The compound's stability in biological matrices and protein binding properties would also require characterization.
Toxicity/Toxicokinetics
Toxicological data for Persicogenin are limited. As a natural product from various plant sources with traditional uses, the compound is generally considered to have a moderate safety profile at the concentrations used in research. However, comprehensive toxicology studies including acute, subchronic, and genotoxicity assessments have not been reported. The compound should be handled with appropriate safety precautions in laboratory settings.
References

[1]. Anticancer efficacies of persicogenin and homoeriodictyol isolated from Rhus retinorrhoea. Process Biochemistry Volume 95, August 2020, Pages 186-196.

Additional Infomation
3',5-Dihydroxy-4',7-Dimethoxyflavanone is an ether compound belonging to the flavonoid class. It has been reported that aucubin is found in peach (Prunus persica), jasmine (Chromolaena odorata), and other organisms with relevant data.
Persicogenin is a natural O-methylated flavonoid with anticancer, antimutagenic, and antileishmanial activities. It inhibits cell proliferation and arrests the cell cycle at G2/M phase, activates Fas/Fas ligand apoptosis, and shows antimycobacterial activity (MIC 174.8 μM). No clinical trials or approvals exist. For research use only.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C17H16O6
Molecular Weight
316.30534
Exact Mass
316.095
CAS #
28590-40-1
PubChem CID
320054
Appearance
White to off-white solid
Density
1.358g/cm3
Boiling Point
574.9ºC at 760 mmHg
Melting Point
163 - 164 °C
Flash Point
215ºC
Vapour Pressure
8.12E-14mmHg at 25°C
Index of Refraction
1.619
LogP
2.821
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
6
Rotatable Bond Count
3
Heavy Atom Count
23
Complexity
427
Defined Atom Stereocenter Count
0
SMILES
COC1=C(C=C(C=C1)C2CC(=O)C3=C(C=C(C=C3O2)OC)O)O
InChi Key
LWBHKKLWSUFUNZ-HNNXBMFYSA-N
InChi Code
InChI=1S/C17H16O6/c1-21-10-6-12(19)17-13(20)8-15(23-16(17)7-10)9-3-4-14(22-2)11(18)5-9/h3-7,15,18-19H,8H2,1-2H3/t15-/m0/s1
Chemical Name
(2S)-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-7-methoxy-2,3-dihydrochromen-4-one
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Note: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture and light.
Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO : ~50 mg/mL (~158.07 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 1.25 mg/mL (3.95 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 12.5 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 1.25 mg/mL (3.95 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 12.5 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

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Solubility in Formulation 3: 1.25 mg/mL (3.95 mM) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), suspension solution; with ultrasonication.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 12.5 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.


 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 3.1615 mL 15.8073 mL 31.6146 mL
5 mM 0.6323 mL 3.1615 mL 6.3229 mL
10 mM 0.3161 mL 1.5807 mL 3.1615 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

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What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
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What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
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  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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Definitions of molecular mass, molecular weight, molar mass and molar weight:
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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

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